Potassium Carbonate → tert-butyl 4-(6-(6-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

HRID 57866노트

반응식

HRID 57866 반응식
[NH:1]1[CH:5]=[C:4]([C:6]2[N:11]=[CH:10][C:9]3[CH:12]=[N:13][N:14]([C:15]4[N:20]=[C:19]([N:21]5[CH2:27][CH2:26][CH2:25][N:24]([C:28]([O-:30])=[O:29])[CH2:23][CH2:22]5)[CH:18]=[CH:17][CH:16]=4)[C:8]=3[CH:7]=2)[CH:3]=[N:2]1.Br[CH2:32][CH:33]1[CH2:35][CH2:34]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:35]1([CH2:34][N:1]2[CH:5]=[C:4]([C:6]3[N:11]=[CH:10][C:9]4[CH:12]=[N:13][N:14]([C:15]5[N:20]=[C:19]([N:21]6[CH2:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:4]([CH3:6])([CH3:5])[CH3:3])=[O:29])[CH2:23][CH2:22]6)[CH:18]=[CH:17][CH:16]=5)[C:8]=4[CH:7]=3)[CH:3]=[N:2]2)[CH2:33][CH2:32]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 867070614-(6-(6-(1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

생성물 1

HCID 86707060tert-butyl 4-(6-(6-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate수율 180.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A suspension of 4-(6-(6-(1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate (200 mg, 0.43 mmol), (bromomethyl)cyclopropane (100 mg, 0.65 mmol), and K2CO3 (120 mg, 0.87 mmol) in DMF (10 mL) was stirred at room temperature for 18 hours. The reaction mixture was extracted with EtOAc (100 mL), washed with brine (50 mL), dried over MgSO4, and concentrated under reduced pressure. The crude was purified by silica gel chromatography using petroleum ether/EtOAc (2/1) as eluting solvents to afford tert-butyl 4-(6-(6-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate as a white solid (200 mg, 89.6%). MS (ESI) m/z: 515 [M+H]+.

후처리

  1. extractionThe reaction mixture was extracted with EtOAc (100 mL)
  2. washwashed with brine (50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified by silica gel chromatography
  6. washas eluting solvents

출처 및 근거

ORD 기록
ord-51ed50cc1eec435c8aaa8fa7eb0269fe
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434725B2

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